Enantioselective synthesis and biological evaluation of a-hydroxylated lactone lignans
M. Sefkow, M. Raschke, and C. Steiner
1Universität Potsdam, Institut für Chemie,
D-14476 Golm, Germany; 2Universität Jena, Lehrstuhl für Ernährungstoxikologie,
Dornburger Strasse 25, D-07743 Jena, Germany
Abstract: A short and efficient synthesis of enantiomerically
pure a-hydroxylated lactone lignans starting
from commercially available diisopropyl malate is presented. Stereoselective
alkylation with various benzyl bromides and saponification yielded the
corresponding succinic acids. Acetalization afforded the dioxolanones,
which were stereoselectively alkylated. Reduction (and deprotection,
where required) yielded the lactone lignans in up to 30 % overall yield.
The inhibition of the proliferation of HT29 colon cancer cells was investigated.
One lignane, bis-2,4,6 trimethylbenzyllactone lignan, was active (IC50
= 35 mM), whereas all other tested lignans
were inactive within the investigated concentration range.
*Pure Appl.Chem. 75,
141419 (2003). An issue of reviews and research papers based on
lectures presented at the 23rd IUPAC International Symposium on the
Chemistry of Natural Products, Florence, Italy, 28 July 2 August 2002.
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